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135729-76-9 molecular structure
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(5S)-3-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-3-azatricyclo[7.3.1.05,13]trideca-1(12),9(13),10-trien-2-one hydrochloride

ChemBase ID: 176210
Molecular Formular: C19H25ClN2O
Molecular Mass: 332.8676
Monoisotopic Mass: 332.16554111
SMILES and InChIs

SMILES:
c12c3cccc1C(=O)N(C[C@H]2CCC3)[C@@H]1C2CCN(C1)CC2.Cl
Canonical SMILES:
O=C1N(C[C@@H]2c3c1cccc3CCC2)[C@H]1CN2CCC1CC2.Cl
InChI:
InChI=1S/C19H24N2O.ClH/c22-19-16-6-2-4-14-3-1-5-15(18(14)16)11-21(19)17-12-20-9-7-13(17)8-10-20;/h2,4,6,13,15,17H,1,3,5,7-12H2;1H/t15-,17+;/m1./s1
InChIKey:
OLDRWYVIKMSFFB-KALLACGZSA-N

Cite this record

CBID:176210 http://www.chembase.cn/molecule-176210.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(5S)-3-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-3-azatricyclo[7.3.1.05,13]trideca-1(12),9(13),10-trien-2-one hydrochloride
IUPAC Traditional name
(5S)-3-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-3-azatricyclo[7.3.1.05,13]trideca-1(12),9(13),10-trien-2-one hydrochloride
Synonyms
(3aS)-2-(3R)-1-Azabicyclo[2.2.2]oct-3-yl-2,3,3a,4,5,6-hexahydro-1H-benz[de]isoquinolin-1-one Hydrochloride
RS 25233-197
(S,R)-Palonosetron Hydrochloride
Palonosetron Hydrochloride
CAS Number
135729-76-9
135729-75-8
PubChem SID
164232120
PubChem CID
18651161

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 18651161 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) 0.109810375  LogD (pH = 7.4) 1.8701022 
Log P 2.5460126  Molar Refractivity 88.5213 cm3
Polarizability 33.791428 Å3 Polar Surface Area 23.55 Å2
Rotatable Bonds Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
MSDS Link
Download expand Show data source
Mechanism of Action
5HT(3) receptor antagonist expand Show data source
Salt Data
HCl expand Show data source
Certificate of Analysis
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Application(s)
Antiemetic used in the prevention and treatment of chemotherapy-induced nausea and vomiting (CINV) expand Show data source

DETAILS

DETAILS

TRC TRC
Toronto Research Chemicals - P165810 external link
The (S,R)-enantiomer of Palonosetron (P165800), a potent and selective antagonist, with 5-HT3 receptor in vitro. An impurity of Palonosetron.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Clark, R.D., et al.: J. Med. Chem., 36, 2645 (1993)
  • • Wong, E.H.F., et al.: Br. J. Pharmacol., 114, 851 (1993)
  • • Grunberg, S.M., et al.: Expert. Opin. Pharmacother., 4, 2297 (1993)
  • • Eisenberg, P., et al.: Ann. Oncol., 15, 330 (1993)
  • • Siddiqui, M.A.A., et al
  • • Eur. Pat., 1991, Syntex, 430 190; CA, 115, 114377b, (synth, pharmacol)
  • • Costall, B. et al., Eur. J. Pharmacol., 1993, 234, 91, (pharmacol)
  • • Clark, R.D. et al., J. Med. Chem., 1993, 36, 2645-2657, (synth, pharmacol, pmr, cryst struct)
  • • Wong, E.H.F. et al., J. Neurochem., 1993, 60, 921; 61, 1927, (pharmacol)
  • • Eglen, R.M. et al., J. Pharmacol. Exp. Ther., 1993, 266, 535, (pharmacol)
  • • Wong, E.H.F. et al., Br. J. Pharmacol., 1995, 114, 851-859; 860-866, (pharmacol)
  • • Graul, A. et al., Drugs of the Future, 1996, 21, 906-910, (rev, synth, pharmacol)
  • • Kowalczyk, B.A. et al., Synthesis, 1996, 816-818; 2000, 1113-1116, (synth, ir, pmr, cmr)
  • • Kowalczyk, B.A. et al., Org. Process Res. Dev., 1997, 1, 117-120, (synth)
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PATENTS

PATENTS

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INTERNET

INTERNET

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